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Ascending to the duchy at the age of thirteen after his father had been assassinated, Charles was expected to carry on his father's leadership against the Burgundians, a French faction which supported the Duke of Burgundy. The latter was never punished for his role in Louis' assassination, and Charles had to watch as his grief-stricken mother Valentina Visconti succumbed to illness not long afterwards. At her deathbed, Charles and the other boys of the family were made to swear the traditional oath of vengeance for their father's murder.

During the early years of his reign as duke, the orphaned Charles was heavily influenced by the guidance of his father-in-law, Bernard VII, Count of Armagnac, for which reason Charles' faction came to be known as the "Armagnacs".

After war with the Kingdom of England was renewed in 1415, Charles was one of the many French noblemen at the Battle of Agincourt on October 25, 1415. He was discovered unwounded but trapped under a pile of corpses, incapacitated by the weight of his own armour.[2] He was taken prisoner by the English, and spent the next twenty-four years being moved from one castle to another in England, including Pontefract Castle the castle where England's king Richard II had been imprisoned and died.[3] The conditions of his confinement were not strict; he was allowed to live more or less in the manner to which he had become accustomed, like so many other captured nobles. However, he was not offered release in exchange for a ransom, since Henry V of England had left instructions forbidding any release: Charles was the natural head of the Armagnac faction and in the line of succession to the French throne, and was therefore deemed too important to be returned to circulation.

It was during these twenty-four years that Charles would write most of his poetry, including melancholy works which seem to be commenting on the captivity itself, such as En la forêt de longue attente.[5]

The majority of his output consists of two books, one in French and the other in English, in the ballade and rondeau fixed forms. Though once controversial, it is now abundantly clear that Charles wrote the English poems which he left behind when he was released in 1440.[6] Unfortunately, his acceptance in the English canon has been slow. A. E. B. Coldiron has argued that the problem relates to his "approach to the erotic, his use of puns, wordplay, and rhetorical devices, his formal complexity and experimentation, his stance or voice: all these place him well outside the fifteenth-century literary milieu in which he found himself in England."[7] In other words, his English poetry sits stylistically between the Middle Ages and the Renaissance.

Finally freed in 1440 by the efforts of his former enemies, Philip the Good and Isabella of Portugal, the Duke and Duchess of Burgundy, he set foot on French soil again after 25 years, "speaking better English than French", according to the English chronicler Raphael Holinshed. Philip the Good had made it a condition that the murder of Louis of Orleans by John the Fearless would not be avenged. Charles agreed to this condition prior to his release.[8] Meeting the Duchess of Burgundy after disembarking, the gallant Charles said: "M'Lady, I make myself your prisoner." At the celebration of his third marriage, with Marie of Cleves, he was created a Knight of the Golden Fleece. His subsequent return to Orléans was marked by a splendid celebration organized by the citizens.

He made a feeble attempt to press his claims to Asti in Italy, before settling down as a celebrated patron of the arts.

The critically acclaimed historical novel Het Woud der Verwachting / Le Forêt de Longue Attente (1949) by Hella Haasse (translated Into English in 1989 under the title "In a Dark Wood Wandering") gives a sympathetic description of the life of Charles, Duke of Orléans.

Charles is also a major character in Margaret Frazer's The Maiden's Tale, a historical mystery and fictional account of a few weeks of his life in England in the autumn of 1439, shortly before his release in 1440.

^John Fox, “Charles d’Orléans, poète anglais?” Romania 86.3 (1965): 433-62, Mary-Jo Arn, ed., Fortunes Stabilnes: Charles of Orleans’s English Book of Love: A Critical Edition (Binghamton, New York: Medieval and Renaissance Texts and Studies, 1994) and N. L. Goodrich, Charles of Orleans: A Study of Themes in his French and in his English Poetry (Geneva: Droz, 1967).

^A. E. B. Coldiron, Canon, Period, and the Poetry of Charles of Orleans: Found in Translation (Ann Arbor: University of Michigan Press, 2000), p. 11.